The first part of this paper uses a historic perspective as a starting point for discussion of the factors that, in the author’s opinion, contributed to Fidel Castro’s rise to power in 1959. The focus of the historic analysis will be on those events that shaped Cuban culture and affected Cuba’s political development from 1492 to 1898. The second part of the paper covers the political and socio-economic events leading to Castro’s ascension to power. Part Three reviews the theories purported to have contributed to the success of “Castroism” and Part Four analyzes the factors that have contributed to its continued survival. In Part Five, the analysis focuses on past US policy and its effect on the Castro regime. The current Cuba policy and proposed scenarios for political change are covered in Part Six turning to an assessment of the current policy in Part 7. The paper concludes with a proposal for a new policy review process in Part 8.